Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides

https://doi.org/10.22146/ijc.70243

Kok Tong Wong(1), Hasnah Osman(2), Thaigarajan Parumasivam(3), Muhammad Solehin Abd Ghani(4), Mohd. Zaheen Hassan(5), Unang Supratman(6), Mohamad Nurul Azmi Mohamad Taib(7*)

(1) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
(2) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
(3) School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
(4) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
(5) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia; College of Pharmacy, King Khalid University, Abha, Kingdom of Saudi Arabia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
(7) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
(*) Corresponding Author

Abstract


Two series of new 3,5-disubstituted-pyrazole-1-carbothioamides (4a-f and 5a-e) were designed and synthesized through condensation reaction between chalcones and thiosemicarbazides under alkaline condition via cyclocondensation reaction. The structures have been elucidated by Fourier-transform infrared (FTIR), High-resolution mass spectrometry (HRMS), one- and two-dimensional nuclear magnetic resonance (NMR) analyses. These compounds were assayed for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Ra using the Tetrazolium microplate assay (TEMA) method. As a result, six compounds (i.e., 4a, 4d, 4f, 5a, 5c, and 5d) showed a weak activity with minimum inhibition concentration (MIC) between 650–530 μM, and other compounds showed no inhibition against MTB. In addition, all tested compounds also did not show any cidal effects for minimum bactericidal concentration (MBC), even at the highest test concentration.


Keywords


3,5-disubstituted-pyrazole-1-carbothioamide; pyrazolines; Mycobacterium tuberculosis; antitubercular agents; anti-mycobacterial

Full Text:

Full Text PDF


References

[1] Harikrishna, N., Isloor, A.M., Ananda, K., Obaid, A., and Fun, H.K., 2016, Synthesis, and antitubercular and antimicrobial activity of 1′-(4-chlorophenyl)pyrazole containing 3,5-disubstituted pyrazoline derivatives, New J. Chem., 40 (1), 73–76.

[2] WHO, 2017, Global Tuberculosis Report 2017, World Health Organization, Geneva.

[3] Corbeet, E., Marston, B., Churchyard, G.J., and De Cock, K.M., 2006, Tuberculosis in sub-Saharan Africa: Opportunities, challenges, and change in the era of antiretroviral treatment, Lancet, 367 (9514), 926–937.

[4] Dixit, S.R., Joshi, S.D., Kulkarni, V.H., Jalalpure, S.S., Kumbar, V.M., Mudaraddi, T.Y., Nadagouda, M.N., and Aminabhavi, T.M., 2017, Pyrrolyl pyrazoline carbaldehydes as enoyl-ACP reductase inhibitors: Design, synthesis and antitubercular activity, Open Med. Chem. J., 11, 92–108.

[5] Yar, M.S., Siddiqui, A.A., and Ali, M.A., 2007, Synthesis and anti-mycobacterial activity of novel heterocycles. J. Serb. Chem. Soc., 72 (1), 5–11.

[6] Oglah, M.K., Mustafa, Y.F., Bashir, M.K., and Jasim, M.H., 2020, Curcumin and its derivatives: A review of their biological activities, Syst. Rev. Pharm., 11 (3), 472–81.

[7] Bashir, M.K., Mustafa, Y.F., and Oglah, M.K., 2020, Antitumor, antioxidant, and antibacterial activities of glycosyl-conjugated compounds: A review, Syst. Rev. Pharm., 11 (4), 175–187.

[8] Mustafa, Y.F., and Abdulaziz, N.T., 2020, Biological potentials of hymecromone-based derivatives: A systematic review. Syst. Rev. Pharm., 11 (11), 438–452.

[9] Mustafa, Y.F., Abdulaziz, N.T., and Jasim, M.H., 2021, 4-Methylumnelliferone and its derived compounds: A brief review of their cytotoxicity, Egypt. J. Chem., 64 (4), 1807–1816.

[10] Cai, D., Zhang, Z.H., Chen, Y., Yan, X.J., Zou, L.J., Wang, Y.X., and Liu, X.Q., 2015, Synthesis, antibacterial and antitubercular activities of some 5H-thiazolo[3,2-a]pyrimidin-5-ones and sulfonic acid derivatives, Molecules, 20 (9), 16419–16343.

[11] Jadhav, S.A., Kulkarni, K.M., Patil, P.B., Dhole, V.R., and Patil, S.S., 2016, Design, synthesis and biological evaluation of some novel pyrazoline derivatives, Pharma Chem., 8 (3), 38–45.

[12] Knorr, L., 1883, Einwirkung von acetessigester auf phenylhydrazin, Ber. Dtsch. Chem. Ges., 16 (2), 2597–2599.

[13] Korrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y.N., Al-Aizari, F.A., and Ansar, M., 2018, Synthesis and pharmacological activities of pyrazole derivatives: A review, Molecules, 23 (1), 134.

[14] Ramirez-Prada, J., Robledo, S.M., Velez, I.D., Crespo, M.D.P., Quiroga, J., Abonia, R., Montoya, A., Svetaz, L., Zacchino, S., and Insuasty, B., 2017, Synthesis of novel quinoline-based 4,5-dihydro-1H-pyrazoles as potential anticancer, Eur. J. Med. Chem., 131, 237–240.

[15] Kumar, G., Tanwar, O., Kumar, J., Akhter, M., Sharma, S., Pillai, C.R., Alam, M.M., and Zama, M.S., 2018, Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study, Eur. J. Med. Chem., 149, 139–147.

[16] Montoya, A., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J., and Insuasty, B., 2014, Synthesis and in vitro antitumor activity of a novel series of 2-pyrazoline derivatives bearing the 4-aryloxy-7-chloroquinoline fragment, Molecules, 19 (11), 18656–18675.

[17] Malhotra, V., Pathak, S., Nath, R., Mukerjee, D., and Shanker, K., 2002, Substituted pyrazolines and their cardiovascular activity, Indian J. Chem. Sect. B, 41 (6), 1310–1313.

[18] Nayak, B.V., Ciftci-Yabanoglu, S., Jadav, S.S., Jagrat, M., Sinha, B.N., Ucar, G., and Jayaprakash, V., 2013, Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-1-carboxylate derivatives, Eur. J. Med. Chem., 69, 762–767.

[19] Upadhyay, S., Tripathi, A.C., Paliwal, S., and Saraf, S.K., 2017, 2-Pyrazoline derivatives in neuropharmacology: Synthesis, ADME prediction, molecular docking and in vivo biological evaluation, EXCLI J., 16, 628–649.

[20] Abid, M., Bhat, A.R., Athar, F., and Azam, A., 2009, Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines, Eur. J. Med. Chem., 44 (1), 417–425.

[21] Beyhan, N., Kocyigit-Kaymakcioglu, B., Gümrü, S., and Aricioglu, F., 2017, Synthesis and anticonvulsant activity of some 2-pyrazolines derived from chalcones, Arabian J. Chem., 10 (Suppl. 2), S2071–S2081.

[22] Bhandari, S., Tripathi, A.C., and Saraf, S.K., 2013, Novel 2-pyrazoline derivatives as potential anticonvulsant agents, Med. Chem. Res., 22 (11), 5290–5296.

[23] Rao, G.S., Kalaichelvan, V.K., and Rao, G.S., 2015, Synthesis and anticonvulsant activity of certain chalcone based pyrazoline compounds, Int. J. Pharm. Res., 5 (8), 179–185.

[24] Ahmad, A., Husain, A., Khan, S.A., Mujeed, M., and Bhandari, A., 2016, Synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives, J. Saudi Chem. Soc., 20 (5), 577–584.

[25] Bhasker, N., Prashanthi, N., and Subba Reddy, B.V., 2015, Piperidine mediated synthesis of new series of prenyloxy chalcones, flavanones and comparative cytotoxic study, Pharm. Lett., 7, 8–13.

[26] Desai, V., Desai, S., Gaonkar, S.N., Palyekar, U., Joshi, S.D., and Dixit, S.K., 2017, Novel quinoxalinyl chalcone hybrid scaffolds as enoyl ACP reductase inhibitors: Synthesis, molecular docking and biological evaluation, Bioorg. Med. Chem. Lett., 27 (10), 2174–2180.

[27] Zhang, L., Wang, A., Wang, W., Huang, Y., Liu, X., Miao, S., Liu, J., and Zhang, T., 2015, Co–N–C Catalyst for C–C coupling reactions: On the catalytic performance and active sites, ACS Catal., 5 (11), 6563–6572.

[28] Mellado, M., Madrid, A., Reyna, M., Weinstein-Oppenheimer, C., Mella, J., Salas, C.O., Sanchez, E., and Cuellar, M., 2018, Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative structure-activity relationship models, Med. Chem. Res., 27 (11), 2414–2425.

[29] Davey, W., and Gwilt, J.R., 1957, Chalcones and related compounds. Part I. Preparation of nitro-, amino-, and halogeno-chalcones, J. Chem. Soc., 0, 1008–1014.

[30] Suwito, H., Jumina, J., Mustofa, M., Pudjiastuti, P., Fanani, M.Z., Kimata-Ariga, Y., Katahira, R., Kawakami, T., Fujiwara, T., Hase, T., Mohd Sirat, H., and Tri Puspaningsih, N.N., 2014, Design and synthesis of chalcone derivatives as inhibitors of the Ferredoxin-Ferredoxin-NADP+ reductase interaction of Plasmodium falciparum: Pursuing new antimalarial agents, Molecules, 19 (12), 21473–21488.

[31] Weber, F.G., and Brosche, K., 1972, Über 1‐Thiocarbamoyl‐und 1‐Carbamoyl‐3, 5‐diaryl‐Δ2‐pyrazoline, Z. Chem., 12 (4), 132–133.

[32] Wan Abdul Wahab, W.N.A., Yahaya, M.L., Md Noor, S.S., and Noor Jamil, N.I., 2016, Direct tetrazolium microplate assay (TEMA) for rapid drug susceptibility test screening of Mycobacterium tuberculosis, Trop. Biomed., 33 (4), 814–823.

[33] Li, X., Hilgers, M., Cunningham, M., Chen, Z., Trzoss, M., Zhang, J., Kohnen, L., Lam, T., Creighton, C., Kedar, G.C., Nelson, K., Kwan, B., Stidham, M., Brown-Driver, V., Shaw, K.J., and Finn, J., 2011, Structure-based design of new DHFR-based antibacterial agents: 7-Aryl-24-diaminoquinazolines, Bioorg. Med. Chem. Lett., 21 (18), 5171–5176.

[34] Aly, S.M., Usman, A., AlZayer, M., Hamdi, G.A., Alarousu, E., and Mohammed, O.F., 2015, Solvent-dependent excited-state hydrogen transfer and intersystem crossing in 2-(2’-hydrogexyphenyl)-benzothiazole, J. Phys. Chem. B, 119 (6), 2596–2603.

[35] Rathod, A.S., Godipurge, S.S., and Biradar, J.S., 2017, Synthesis of indole, coumarinyl and pyridinyl derivatives of isoniazid as potent antitubercular and antimicrobial agents and their molecular docking studies, Int. J. Pharm. Pharm. Sci., 9 (12), 233–240.



DOI: https://doi.org/10.22146/ijc.70243

Article Metrics

Abstract views : 1211 | views : 695


Copyright (c) 2022 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.